TW200911760A - Compounds and uses thereof - Google Patents
Compounds and uses thereof Download PDFInfo
- Publication number
- TW200911760A TW200911760A TW097122555A TW97122555A TW200911760A TW 200911760 A TW200911760 A TW 200911760A TW 097122555 A TW097122555 A TW 097122555A TW 97122555 A TW97122555 A TW 97122555A TW 200911760 A TW200911760 A TW 200911760A
- Authority
- TW
- Taiwan
- Prior art keywords
- amino
- propyl
- alkyl
- group
- carboxamide
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 318
- 150000003839 salts Chemical class 0.000 claims abstract description 70
- 239000002243 precursor Substances 0.000 claims abstract description 36
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 805
- -1 4-amino-8-(3,5-dimethoxyphenyl)-N- Propyl-porphyrin-3-carboxamide Chemical compound 0.000 claims description 310
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 234
- 125000003118 aryl group Chemical group 0.000 claims description 212
- 125000001072 heteroaryl group Chemical group 0.000 claims description 180
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 162
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 143
- 150000001412 amines Chemical class 0.000 claims description 134
- 150000003857 carboxamides Chemical class 0.000 claims description 113
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 89
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 86
- 125000003545 alkoxy group Chemical group 0.000 claims description 85
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 83
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 73
- 125000001424 substituent group Chemical group 0.000 claims description 72
- 125000005843 halogen group Chemical group 0.000 claims description 71
- 125000001188 haloalkyl group Chemical group 0.000 claims description 69
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 56
- 125000003342 alkenyl group Chemical group 0.000 claims description 49
- 125000000623 heterocyclic group Chemical group 0.000 claims description 49
- 125000000304 alkynyl group Chemical group 0.000 claims description 44
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 37
- 125000003282 alkyl amino group Chemical group 0.000 claims description 36
- 125000004076 pyridyl group Chemical group 0.000 claims description 36
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 29
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 28
- 125000003277 amino group Chemical group 0.000 claims description 28
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 27
- 239000000460 chlorine Substances 0.000 claims description 27
- 238000001727 in vivo Methods 0.000 claims description 27
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 26
- 238000011282 treatment Methods 0.000 claims description 25
- 239000003814 drug Substances 0.000 claims description 23
- 150000004032 porphyrins Chemical class 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
- 229910052701 rubidium Inorganic materials 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 15
- 150000002923 oximes Chemical class 0.000 claims description 15
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 15
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 14
- 239000007789 gas Substances 0.000 claims description 14
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 14
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 13
- 125000005265 dialkylamine group Chemical group 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 12
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000000524 functional group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 9
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 229910052705 radium Inorganic materials 0.000 claims description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 239000002689 soil Substances 0.000 claims description 7
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 6
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 claims description 6
- 229910052786 argon Inorganic materials 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 238000003776 cleavage reaction Methods 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 230000007017 scission Effects 0.000 claims description 6
- 239000004202 carbamide Substances 0.000 claims description 5
- 230000001149 cognitive effect Effects 0.000 claims description 5
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 4
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 4
- 229930004069 diterpene Natural products 0.000 claims description 4
- 239000000839 emulsion Substances 0.000 claims description 4
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 4
- LBTAXVIGKZQJMU-UHFFFAOYSA-N n-propyldecan-1-amine Chemical compound CCCCCCCCCCNCCC LBTAXVIGKZQJMU-UHFFFAOYSA-N 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- LUNUNJFSHKSXGQ-UHFFFAOYSA-N 4-Aminoindole Chemical compound NC1=CC=CC2=C1C=CN2 LUNUNJFSHKSXGQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000007942 carboxylates Chemical class 0.000 claims description 3
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 3
- USGYNNGHZHARJS-UHFFFAOYSA-N n-prop-2-enyldecan-1-amine Chemical compound CCCCCCCCCCNCC=C USGYNNGHZHARJS-UHFFFAOYSA-N 0.000 claims description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- LOOFQKJVFBSMLL-UHFFFAOYSA-N 23-methyl-21h-porphyrin Chemical compound CN1C(C=C2C=CC(=N2)C=C2C=CC(N2)=C2)=CC=C1C=C1C=CC2=N1 LOOFQKJVFBSMLL-UHFFFAOYSA-N 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 5
- 235000013877 carbamide Nutrition 0.000 claims 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- QCWPXJXDPFRUGF-UHFFFAOYSA-N N1C=2C=C(N=3)C=CC=3C=C(N3)C=CC3=CC(=N3)C=CC3=CC1=CC=2C1=CC=CC=C1 Chemical compound N1C=2C=C(N=3)C=CC=3C=C(N3)C=CC3=CC(=N3)C=CC3=CC1=CC=2C1=CC=CC=C1 QCWPXJXDPFRUGF-UHFFFAOYSA-N 0.000 claims 2
- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 claims 2
- 229960001967 tacrolimus Drugs 0.000 claims 2
- QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 claims 2
- XDEHMKQLKPZERH-BYPYZUCNSA-N (2s)-2-amino-3-methylbutanamide Chemical compound CC(C)[C@H](N)C(N)=O XDEHMKQLKPZERH-BYPYZUCNSA-N 0.000 claims 1
- QUGUFLJIAFISSW-UHFFFAOYSA-N 1,4-difluorobenzene Chemical compound FC1=CC=C(F)C=C1 QUGUFLJIAFISSW-UHFFFAOYSA-N 0.000 claims 1
- KEVRHVMWBKFGLO-UHFFFAOYSA-N 2,4-dimethoxypyrimidine Chemical compound COC1=CC=NC(OC)=N1 KEVRHVMWBKFGLO-UHFFFAOYSA-N 0.000 claims 1
- IBTGEEMBZJBBSH-UHFFFAOYSA-N 2,6-dimethoxypyridine Chemical compound COC1=CC=CC(OC)=N1 IBTGEEMBZJBBSH-UHFFFAOYSA-N 0.000 claims 1
- VQBINKFJNGWISU-UHFFFAOYSA-N 2-borylporphyrin Chemical compound [N]1C2=CC=C1C=C(N1)C=C(B)C1=CC([N]1)=CC=C1C=C(N1)C=CC1=C2 VQBINKFJNGWISU-UHFFFAOYSA-N 0.000 claims 1
- UHLKYVNSNIWKGX-UHFFFAOYSA-N 2-pyridin-3-ylguanidine Chemical compound NC(=N)NC1=CC=CN=C1 UHLKYVNSNIWKGX-UHFFFAOYSA-N 0.000 claims 1
- DANLZOIRUUHIIX-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F DANLZOIRUUHIIX-UHFFFAOYSA-N 0.000 claims 1
- XQABVLBGNWBWIV-UHFFFAOYSA-N 4-methoxypyridine Chemical compound COC1=CC=NC=C1 XQABVLBGNWBWIV-UHFFFAOYSA-N 0.000 claims 1
- WUDIFKJDBNRHOF-UHFFFAOYSA-N COC1=C(C=CC(=C1)OC)C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N1)=C2 Chemical compound COC1=C(C=CC(=C1)OC)C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N1)=C2 WUDIFKJDBNRHOF-UHFFFAOYSA-N 0.000 claims 1
- 101100181929 Caenorhabditis elegans lin-3 gene Proteins 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 1
- SFIHQZFZMWZOJV-UHFFFAOYSA-N Linolsaeure-amid Natural products CCCCCC=CCC=CCCCCCCCC(N)=O SFIHQZFZMWZOJV-UHFFFAOYSA-N 0.000 claims 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 1
- QNZPTWPLKHMSMK-UHFFFAOYSA-N NN.NN.C(CC)NN Chemical compound NN.NN.C(CC)NN QNZPTWPLKHMSMK-UHFFFAOYSA-N 0.000 claims 1
- 239000005642 Oleic acid Substances 0.000 claims 1
- JUVLOHBIAARAPO-UHFFFAOYSA-N Tacamine Natural products C12=CC=CC=C2N2C(O)(C(=O)OC)CC3CC(CC)CN4C3C2=C1CC4 JUVLOHBIAARAPO-UHFFFAOYSA-N 0.000 claims 1
- 229940045799 anthracyclines and related substance Drugs 0.000 claims 1
- NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical compound NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 0.000 claims 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical group [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims 1
- 125000005026 carboxyaryl group Chemical group 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 claims 1
- 150000007946 flavonol Chemical class 0.000 claims 1
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 claims 1
- 235000011957 flavonols Nutrition 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims 1
- SFIHQZFZMWZOJV-HZJYTTRNSA-N linoleamide Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(N)=O SFIHQZFZMWZOJV-HZJYTTRNSA-N 0.000 claims 1
- 229930182817 methionine Natural products 0.000 claims 1
- JUVLOHBIAARAPO-BJIKLQPUSA-N methyl (13R,15R,17R,19R)-13-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate Chemical compound C12=CC=CC=C2N2[C@](O)(C(=O)OC)C[C@H]3C[C@@H](CC)CN4[C@H]3C2=C1CC4 JUVLOHBIAARAPO-BJIKLQPUSA-N 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims 1
- 125000001680 trimethoxyphenyl group Chemical group 0.000 claims 1
- 230000010415 tropism Effects 0.000 claims 1
- 210000003462 vein Anatomy 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 60
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 210
- 238000000034 method Methods 0.000 description 140
- 239000007787 solid Substances 0.000 description 117
- 238000004128 high performance liquid chromatography Methods 0.000 description 114
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 110
- 239000002585 base Substances 0.000 description 109
- 101150041968 CDC13 gene Proteins 0.000 description 88
- 235000019439 ethyl acetate Nutrition 0.000 description 85
- 238000005481 NMR spectroscopy Methods 0.000 description 73
- 238000006243 chemical reaction Methods 0.000 description 70
- 229910001868 water Inorganic materials 0.000 description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 54
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 47
- 239000000243 solution Substances 0.000 description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 125000004429 atom Chemical group 0.000 description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 20
- 102000005962 receptors Human genes 0.000 description 20
- 108020003175 receptors Proteins 0.000 description 20
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 16
- 230000000694 effects Effects 0.000 description 16
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 16
- 208000019901 Anxiety disease Diseases 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 201000010099 disease Diseases 0.000 description 15
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 15
- 239000010410 layer Substances 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 239000001257 hydrogen Substances 0.000 description 14
- 239000002207 metabolite Substances 0.000 description 14
- 239000003960 organic solvent Substances 0.000 description 14
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- 238000006467 substitution reaction Methods 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
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- 239000007788 liquid Substances 0.000 description 13
- 230000002829 reductive effect Effects 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
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- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 description 1
- WCTNXGFHEZQHDR-UHFFFAOYSA-N valencene Natural products C1CC(C)(C)C2(C)CC(C(=C)C)CCC2=C1 WCTNXGFHEZQHDR-UHFFFAOYSA-N 0.000 description 1
- BDIAUFOIMFAIPU-UHFFFAOYSA-N valepotriate Natural products CC(C)CC(=O)OC1C=C(C(=COC2OC(=O)CC(C)C)COC(C)=O)C2C11CO1 BDIAUFOIMFAIPU-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 1
- 229960004688 venlafaxine Drugs 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 230000001018 virulence Effects 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- HUNXMJYCHXQEGX-UHFFFAOYSA-N zaleplon Chemical compound CCN(C(C)=O)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)C#N)=C1 HUNXMJYCHXQEGX-UHFFFAOYSA-N 0.000 description 1
- 229960004010 zaleplon Drugs 0.000 description 1
- 229960001366 zolazepam Drugs 0.000 description 1
- 229960001360 zolmitriptan Drugs 0.000 description 1
- ULSDMUVEXKOYBU-ZDUSSCGKSA-N zolmitriptan Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1C[C@H]1COC(=O)N1 ULSDMUVEXKOYBU-ZDUSSCGKSA-N 0.000 description 1
- 229940039925 zyprexa Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/502—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with carbocyclic ring systems, e.g. cinnoline, phthalazine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94488307P | 2007-06-19 | 2007-06-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200911760A true TW200911760A (en) | 2009-03-16 |
Family
ID=39811856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW097122555A TW200911760A (en) | 2007-06-19 | 2008-06-17 | Compounds and uses thereof |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US20080318925A1 (fr) |
| EP (1) | EP2167091A1 (fr) |
| JP (1) | JP2010530406A (fr) |
| KR (1) | KR20100039340A (fr) |
| AR (1) | AR067028A1 (fr) |
| AU (1) | AU2008264985A1 (fr) |
| BR (1) | BRPI0813253A2 (fr) |
| CA (1) | CA2691648A1 (fr) |
| CL (1) | CL2008001837A1 (fr) |
| EC (1) | ECSP109885A (fr) |
| IL (1) | IL202496A0 (fr) |
| PE (1) | PE20090771A1 (fr) |
| TW (1) | TW200911760A (fr) |
| UY (1) | UY31161A1 (fr) |
| WO (1) | WO2008155573A1 (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007073283A1 (fr) * | 2005-12-20 | 2007-06-28 | Astrazeneca Ab | Derives substitues de la cinnoline en tant que modulateurs du recepteur du gabaa et leur procede de synthese |
| US7465795B2 (en) * | 2005-12-20 | 2008-12-16 | Astrazeneca Ab | Compounds and uses thereof |
| WO2010123441A1 (fr) * | 2009-04-21 | 2010-10-28 | Astrazeneca Ab | Forme cristalline de l'hydrogénosulfate de 4-amino-8-(2-fluoro-6-méthoxy-phényl)-n-propylcinnoline-3-carboxamide pour le traitement de troubles liés à l'anxiété |
| WO2011021979A1 (fr) * | 2009-08-18 | 2011-02-24 | Astrazeneca Ab | Composés de cinnoline, leur préparation et leur utilisation |
| CN105541759A (zh) * | 2016-01-07 | 2016-05-04 | 美吉斯制药(厦门)有限公司 | 一种制备沃替西汀的新方法 |
| CN116589521B (zh) * | 2019-01-08 | 2025-07-11 | 成都康弘药业集团股份有限公司 | 甾体类化合物、用途及其制备方法 |
| US12139498B1 (en) * | 2023-04-18 | 2024-11-12 | Vanderbilt University | Positive allosteric modulators of the muscarinic acetylcholine receptor M4 |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4230713A (en) * | 1979-01-19 | 1980-10-28 | Ici Americas Inc. | Heterocyclic tetrahydro-1-alkyl-4-oxo-1H-imidazol-2-ylidene urea and phenyl esters of tetrahydro-1-alkyl-4-oxo-1H-imidazol-2-ylidene carbamic acid compounds |
| GB8310266D0 (en) * | 1982-05-12 | 1983-05-18 | Ici America Inc | Pyrazolopyridine compounds |
| US4552883A (en) * | 1982-06-15 | 1985-11-12 | Ici Americas Inc. | Pyrazolo[3,4-b]pyridine carboxylic acid esters and their pharmaceutical use |
| US4563525A (en) * | 1983-05-31 | 1986-01-07 | Ici Americas Inc. | Process for preparing pyrazolopyridine compounds |
| GB8329531D0 (en) * | 1983-11-04 | 1983-12-07 | Ici America Inc | Pyrazolopyridine cycloalkanones |
| GB8421116D0 (en) * | 1984-08-20 | 1984-09-26 | Ici America Inc | Alkynyl derivatives |
| GB8425104D0 (en) * | 1984-10-04 | 1984-11-07 | Ici America Inc | Amide derivatives |
| GB8513639D0 (en) * | 1985-05-30 | 1985-07-03 | Ici America Inc | Cinnoline compounds |
| GB8610980D0 (en) * | 1986-05-06 | 1986-06-11 | Ici America Inc | Heterocyclic fused tricyclic compounds |
| DD249011A5 (de) * | 1986-06-20 | 1987-08-26 | Ici Americas Inc,Us | Verfahren zur herstellung von cinnolin-verbindungen |
| GB8702288D0 (en) * | 1987-02-02 | 1987-03-11 | Erba Farmitalia | Cinnoline-carboxamides |
| DE68902490T2 (de) * | 1988-02-09 | 1992-12-24 | Ici America Inc | Pharmazeutische zusammensetzung. |
| US4925844A (en) * | 1988-02-09 | 1990-05-15 | Ici Americas Inc. | Antagonizing the pharmacological effects of a benzodiazepine receptor agonist |
| US5240934A (en) * | 1990-10-19 | 1993-08-31 | Ss Pharmaceutical Co., Ltd. | Quinoline derivatives |
| US5190951A (en) * | 1990-10-19 | 1993-03-02 | Ss Pharmaceutical Co., Ltd. | Quinoline derivatives |
| US5480883A (en) * | 1991-05-10 | 1996-01-02 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Bis mono- and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| US5750088A (en) * | 1993-03-30 | 1998-05-12 | The Dupont Merck Pharmaceutical Company | Stable hydrazones linked to a peptide moiety as reagents for the preparation of radiopharmaceuticals |
| US6140265A (en) * | 1995-07-25 | 2000-10-31 | Clariant Gmbh | Catalyst for cross-coupling reactions |
| DE19620023C2 (de) * | 1996-05-17 | 2001-03-08 | Celanese Chem Europe Gmbh | Verfahren zur Herstellung von Phosphinat- oder Phosphonatgruppen enthaltenden tertiären Phosphanen und neue Phosphinatgruppen enthaltende tertiäre Phosphane |
| PT1064243E (pt) * | 1998-03-18 | 2003-03-31 | Ciba Sc Holding Ag | Reaccoes de acoplamento com catalisadores de paladio |
| US6362216B1 (en) * | 1998-10-27 | 2002-03-26 | Array Biopharma Inc. | Compounds which inhibit tryptase activity |
| DE19916222A1 (de) * | 1999-04-10 | 2000-10-19 | Aventis Res & Tech Gmbh & Co | Verfahren zur Herstellung von Biarylen |
| FR2801584B1 (fr) * | 1999-11-26 | 2003-05-30 | Rhodia Chimie Sa | Procede de preparation d'un compose polyaromatique |
| US6984756B2 (en) * | 2000-05-19 | 2006-01-10 | Eli Lilly And Company | Process for preparing biphenyl compounds |
| RU2279428C2 (ru) * | 2000-09-18 | 2006-07-10 | Эйсай Ко., Лтд. | Производные пиридазинона и триазинона и их применение в качестве фармацевтических препаратов |
| US20050113283A1 (en) * | 2002-01-18 | 2005-05-26 | David Solow-Cordero | Methods of treating conditions associated with an EDG-4 receptor |
| US20040102360A1 (en) * | 2002-10-30 | 2004-05-27 | Barnett Stanley F. | Combination therapy |
| CA2502429A1 (fr) * | 2002-10-31 | 2004-05-21 | Amgen Inc. | Agents anti-inflammatoires |
| US20040167165A1 (en) * | 2003-01-16 | 2004-08-26 | Geetha Shankar | Methods of treating conditions associated with an Edg-7 receptor |
| AR043633A1 (es) * | 2003-03-20 | 2005-08-03 | Schering Corp | Ligandos de receptores de canabinoides |
| WO2006124996A2 (fr) * | 2005-05-17 | 2006-11-23 | Supergen, Inc. | Inhibiteurs de la kinase de type polo 1 |
| GB0521563D0 (en) * | 2005-10-21 | 2005-11-30 | Glaxo Group Ltd | Novel compounds |
| US7465795B2 (en) * | 2005-12-20 | 2008-12-16 | Astrazeneca Ab | Compounds and uses thereof |
| WO2007073283A1 (fr) * | 2005-12-20 | 2007-06-28 | Astrazeneca Ab | Derives substitues de la cinnoline en tant que modulateurs du recepteur du gabaa et leur procede de synthese |
-
2008
- 2008-06-17 AR ARP080102574A patent/AR067028A1/es unknown
- 2008-06-17 TW TW097122555A patent/TW200911760A/zh unknown
- 2008-06-18 JP JP2010512777A patent/JP2010530406A/ja active Pending
- 2008-06-18 UY UY31161A patent/UY31161A1/es unknown
- 2008-06-18 WO PCT/GB2008/050457 patent/WO2008155573A1/fr not_active Ceased
- 2008-06-18 AU AU2008264985A patent/AU2008264985A1/en not_active Abandoned
- 2008-06-18 CA CA002691648A patent/CA2691648A1/fr not_active Abandoned
- 2008-06-18 BR BRPI0813253-4A2A patent/BRPI0813253A2/pt not_active IP Right Cessation
- 2008-06-18 US US12/141,240 patent/US20080318925A1/en not_active Abandoned
- 2008-06-18 KR KR1020107001092A patent/KR20100039340A/ko not_active Withdrawn
- 2008-06-18 EP EP08806634A patent/EP2167091A1/fr not_active Withdrawn
- 2008-06-19 PE PE2008001053A patent/PE20090771A1/es not_active Application Discontinuation
- 2008-06-19 CL CL2008001837A patent/CL2008001837A1/es unknown
-
2009
- 2009-12-03 IL IL202496A patent/IL202496A0/en unknown
-
2010
- 2010-01-19 EC EC2010009885A patent/ECSP109885A/es unknown
- 2010-03-15 US US12/723,834 patent/US20100184738A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CA2691648A1 (fr) | 2008-12-24 |
| WO2008155573A1 (fr) | 2008-12-24 |
| ECSP109885A (es) | 2010-02-26 |
| BRPI0813253A2 (pt) | 2014-12-30 |
| JP2010530406A (ja) | 2010-09-09 |
| CL2008001837A1 (es) | 2009-06-26 |
| KR20100039340A (ko) | 2010-04-15 |
| US20080318925A1 (en) | 2008-12-25 |
| IL202496A0 (en) | 2010-06-30 |
| EP2167091A1 (fr) | 2010-03-31 |
| UY31161A1 (es) | 2009-01-30 |
| AU2008264985A1 (en) | 2008-12-24 |
| AR067028A1 (es) | 2009-09-30 |
| PE20090771A1 (es) | 2009-07-23 |
| US20100184738A1 (en) | 2010-07-22 |
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